By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Marc Gross

Risk has been my path throughout my life. In my younger days, the risks I took would be the kinds you warn people about, the kind you maybe don’t want to dwell on or put out there for the world to see. But those risks are part of my story and play a role in how I got to where I am. I’ll just say this about those years; In my late teens and 20’s I didn’t think I’d make it to 30 and I took every avenue I could find to ensure it. Survival instinct got the better of me and I wake up grateful for that every single day. Read more>>

Amber Kitayama

I would say my biggest risk was trusting in myself,going and truly believing in my capabilities. Not everyone can handle failure or failing. Not everyone can take those short commings and turn them into a positive. So taking the risk and actually believing in yourself is scary. But with that being said. It’s the most empowering thing a person can do for oneself. Read more>>

Hetty (Christine) Hettinger

Risk is a big part of being a traveling tattoo artist. Every time I go somewhere new, there’s a chance I might not have enough clients to cover my expenses—flights, hotels, studio space. It’s stressful, but taking those risks has opened up incredible opportunities for me. I’ve met amazing people, expanded my skills, and built connections I wouldn’t have otherwise. Read more>>

Dana Schaeffer

For me, risk is about growth and possibility. I see it as an opportunity to push myself beyond what I think I’m capable of and to prove that with determination, anything is possible. One of the biggest risks I’ve taken was leaving my comfortable 9-5 corporate job — a job I had dreamed of since I was a child. I stepped away from that security to bet on myself, with no job lined up, to focus on my own projects and passions. It was a leap of faith, but I knew it was what I needed to grow and align with my true purpose. Read more>>

Grace Kim

I see risk as part of life—almost like a game where every decision we make involves some level of uncertainty. Whether it’s a small choice or a big move, there’s always a risk factor. Some people are great at planning and strategizing to minimize risks, while others might just dive in and hope for the best. But no matter what business you’re in, especially if you’re running your own, taking risks is unavoidable. Read more>>

Romiah Puertollano

I think risk lies within how deep your faith is and how much you trust in the Universe and God or whom and whatever you believe in. Within my career I have dived into things blind. Just running on the faith that no matter what happens and no matter the outcome it will all work out for me. The belief in your own talent and what you can offer has to be stronger than your fears. Plus there is no growth in staying in your comfort zone. Risks build character, makes you wiser and builds so much confidence within yourself. Read more>>

Nicole Welch | Production Manager & Owner of Sighs From Production Management, LLC

Risk is bold, scary, uncomfortable, and life-changing. Without taking risks I would not be where I am today. I’d likely be back home in Michigan, but I’ve always wanted more for my life and career. I knew God wanted more for me, and I’ve continued to follow the journey I believe was written for me. Risk took me to New York with about $800 in my pocket (My rent was $400), not knowing a soul, and sleeping on the peeling faux leather couch of one of my brother’s friends for a year while I worked an unpaid network TV internship and retail jobs to make ends meet. Risk and faith told me to stop working jobs that were crutches and trust that working in the entertainment industry would work out for me, so I quit working at the Gap Outlet in Brooklyn with no job prospects. Read more>>

Tony Tovar | Hair Colorist

I personally believe you’ve got to risk it to get the biscuit! When I was in cosmetology school, my partner, Abraham introduced me to celebrity vocal coach Stevie Mackey. Stevie loved my platinum blonde hair at the time and asked me to color his hair. I was only about two months into school, so I didn’t feel very confident. Despite the doubts in my head, I said yes, knowing the opportunity was there for a reason. That one decision opened so many doors for me, and I’ve been doing Stevie’s hair for five years now. It taught me that sometimes, saying yes to the unknown can lead to opportunities beyond what you can imagine. That opportunity ultimately led to me earning a spot at one of Los Angeles’ most esteemed salons, Roil Salon. Read more>>

Sheyda Entezari | CEO & Aesthetician

I am a true believer in taking risks. If you know me personally, you know! I put a lot on the line to open my practice. You will never know your potential by sitting in your doubts, start working towards your goals and take the risk. Read more>>

Kelly Tourgeman | Jewelry Designer & Pilates Instructor

If you were to ask all of my friends if I was a risk-taker, they would probably say no, however, they would be wrong. I don’t sky-dive or bungee jump, but I go all in when it comes to realize my ideas. Risk one, why not pursue a Master’s Degree in English and a Pilates instructor certification at the same time? Yes, done. Risk two, why answer an email from a chiropractor that wanted me to start a Pilates studio in his practice? Yes, done. Why buy my own building for my own Pilates space when I had a two year old baby? Yes, done. Why did I decide that a chronic illness (MS) would not limit me? Well, ask me on any given day and I may give you a different answer, but I did start yet another business–an online and retail jewelry business, with me as the designer, seller and discerning buyer of vintage gems. Read more>>

Nick Griffith | Creator / Performer

I believe taking risks is a large part of what generates personal growth.

As an entertainer and an artist it is necessity.

As an artist, before you really hit a stride, you you must find the boundaries of safety and test them.

You have to make bad work. You have to make ambitious immature work. Write bad jokes and bad, screenplays. Not really bad, just artistically immature. Flashes of promise will be there.

What works can be so surprising when we start, we have to take risks to create adversity and give our work room to grow. Read more>>

Taylor Joshua Rankin | Composer & Filmmaker

In my experience there’s an ignorance one must have in attempting to accomplish anything. Sometimes this means making what can feel like very stupid decisions, creatively, financially, personally, holistically. If the idea is to achieve a goal, or to make a thing, risk can be simply the act of working to accomplish that goal. So much art these days, particularly because of the way we’ve been geared to engage with art through its branding and marketing, is made out to exist for a “reason”. “The reason” I made this is because of this and this”, etc. I’ve always tried to engage with art through a lens of curiosity and tinkering rather than a lens through which a purpose is gained (outside of the purpose being of course to complete the project). Read more>>

Lu Li | Film Editor

Risk has been a constant in my career, and I’ve learned to see it as both a challenge and an opportunity. Film editing is not only a technical craft but also an artistic choice, demanding bold decisions—whether it’s experimenting with unconventional structures or navigating new industry dynamics. The rise of AI in post-production, such as auto-editing, sound design, AI composition, and VFX generation, has introduced uncertainty but also opportunities to enhance my craft. Read more>>